Chattanooga Choo Choo

At the Chattanooga Choo Choo, Alonzo Dillard's 75th birthday is celebrated with his daughter Estelle, granddaughter Jennie, Jennie's fiancé Paul, and staff. Bert Waters arrives late because he has been with his girlfriend Maggie Jones, whom he plans to marry after divorcing Estelle. The mood is festive but tense as Alonzo dispenses cool hospitality toward Bert.

Shortly after Bert's arrival, Alonzo collapses and is buried in a Boxcar as part of the ceremony. When the will is read, it reveals his fortunes: Woodrow receives $100,000 and a pension, Jennie stands to inherit $5,000,000, and Estelle gets the property and company. The moment reshapes family loyalties and sets Bert's future in motion.

The will requires Bert to restore and operate the historic Chattanooga Choo Choo locomotive and full train from Pennsylvania Station in New York to Chattanooga, following the timetable. He must arrive exactly 24 hours later to secure the $1,000,000 prize. The task tests his nerve, resourcefulness, and reliability under pressure.

On his way to tell Maggie the plan, Bert is harassed by a biker gang that mocks his lavender obsession. He orders his bodyguard Hashimoto to destroy their Harley-Davidson, turning the moment into a rapid, public showdown.

Bert converts the trip into a boisterous publicity stunt for his new football team, coached by Newt Newton, in an effort to win the city's stadium bid. The spectacle foresees a grand wedding for Jennie and the Duke at the Railway Museum, tying the train's journey to a future ceremony.

Sam Cartwright and Paul Cartwright board the train, with Estelle left behind in a phone booth. Maggie sneaks onto the train and begins pursuing Newt, while Hashimoto forgets Bert's luggage, increasing the traveling chaos.

Sam discovers Bert has bribed an inside man to remove the Cartwright bid and carry it along on the train. The revelation explains Bert's confidence but introduces a corrupt element to the competition and its consequences.

Norman the Fireman and Pee Wee the Engineer are rusty and struggle to communicate, causing a 15-minute delay. Bert orders the crew to skip Philadelphia, a choice that upends Estelle's plans to board and further complicates the timetable.

Paul speaks with Jennie, who suspects the engagement photos may be fake. Meanwhile, the two twins from the photo turn out to be part of the team’s cheer squad and are aboard the train.

Football player Jim-Bob plays a prank on Bert with a laxative, forcing him to toss his pants out the window. He must deliver a whistle-stop press conference in Washington, DC while wearing a skirt, and Hashimoto restrains Sam so he cannot disembark.

Maggie discovers Jim-Bob has drilled a peephole into the cheerleaders' compartment. She starts plotting a distraction, using her mascara to sabotage the hole and steer attention away from the crew.

Maggie's plan intensifies as Jim-Bob's eyelid becomes glued to the wall after a confrontation with the cheerleaders, triggering the emergency brake and sending the train further off schedule.

Maggie coordinates an ultralight plane to land on the train so Sam can deliver his bid in time, while Newt takes Sam's place onboard. Sam uses Woodrow's radio to request more speed from the locomotive, and the train moves ahead of schedule.

Maggie reveals the Duke’s true identity as Memphis con artist Bob Shoemaker. The team confronts him, forcing a confession in front of Jennie and the Trainspotters, which allows Jennie and Paul to reconcile.

The group faces a biker gang roadblock that delays Bert as he bargains with the executor. They arrive two minutes late, costing the bid, and Hashimoto resigns after a racial slur is hurled. Bert walks back to retrieve his car, and a cheerleader's interest hints he may marry her for money.